Where to Entertain in the Flatiron District

Lunch for Two: A few blocks south of Madison Square Park is Bar Stuzzichini, a trattoria with handsome wood accents. Take a seat at the bar for tasty bites like spicy salumi and fried artichoke, or sit at one of the tables for heartier dishes, such as stuffed swordfish with Sicilian pesto and gnocchi with guanciale, tomatoes, onions, and chilies.

Drinks for Four: On the second floor of the restaurant Punch, Wined Up focuses on small vintners, with 150 selections by the bottle and 30 by the glass. A long bar and groups of tables sit amid extensive wine displays. Nibble on assorted cheeses and meats, pizzas, and fondues.A Private Dinner for 20: Take an informal group to new barbecue joint Hill Country, which has an alcove on the lower level that can be partitioned for 20. Open since June, the restaurant serves its Texan fare family-style (and on butcher paper). While diners here order and pay at the counter, private parties can choose from a set menu.

Cocktails for 100: Assemble a group for cocktails or dinner at the richly decorated Prince George Ballroom, which has neo-Renaissance details such as gilded columns and carved ceilings. The ballroom has an adjoining gallery space—a study in contrasts, with a white, modern look.